Ketone bodies are small compounds derived from fatty acids that behave as an alternative mitochondrial energy source when insulin levels are low, such as during fasting or strenuous exercise. In addition to the metabolic function of... more
Ketone bodies are small compounds derived from fatty acids that behave as an alternative mitochondrial energy source when insulin levels are low, such as during fasting or strenuous exercise. In addition to the metabolic function of ketone bodies, they also have several signaling functions separate from energy production. In this perspective, we review the main current data referring to ketone bodies in correlation with nutrition and metabolic pathways as well as to the signaling functions and the potential impact on clinical conditions. Data were selected following eligibility criteria accordingly to the reviewed topic. We used a set of electronic databases (Medline/PubMed, Scopus, Web of Sciences (WOS), Cochrane Library) for a systematic search until July 2022 using MeSH keywords/terms (i.e., ketone bodies, BHB, acetoacetate, inflammation, antioxidant, etc.). The literature data reported in this review need confirmation with consistent clinical trials that might validate the resul...
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I poliesteri sono una categoria di polimeri con un’ampia gamma di applicazioni commerciali e particolarmente indicati per la produzione di materiali da imballaggio e rivestimento. Il crescente interesse verso nuovi materiali... more
I poliesteri sono una categoria di polimeri con un’ampia gamma di applicazioni commerciali e particolarmente indicati per la produzione di materiali da imballaggio e rivestimento. Il crescente interesse verso nuovi materiali ecocompatibili e biodegradabili sta stimolando l’interesse del mondo accademico e industriale verso l’impiego di intermedi derivati da risorse rinnovabili per la produzione di polimeri alternativi a quelli tradizionalmente ottenuti da monomeri di origine fossile.1 Nel presente contributo, proponiamo l’impiego del 5,5’-diidrossimetil furoino (DHMF), un triolo ottenuto dalla condensazione benzoinica organocatalizzata del 5-idrossimetilfurfurale (HMF),2 come comonomero in combinazione col dietil succinato per la sintesi di poliesteri completamente derivati da fonti di carbonio rinnovabile. Un ulteriore aspetto di sostenibilità del processo proposto, sta nel fatto che la policondensazione è stata condotta in blande condizioni di temperatura grazie all’uso della lipasi B da Candida antarctica (CAL-B) come catalizzatore. Come atteso inoltre, la selettività dell’enzima ha permesso di ottenere oligomeri lineari, nei quali solo gli ossidrili primari del DHMF sono stati interessati dalla policondensazione, mentre gli ossidrili secondari restano liberi e a disposizione per ulteriori elaborazioni sintetiche. Le strutture dei nuovi oligomeri così ottenuti sono state determinate attraverso studi NMR e analisi HPLC-MS
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Enantiomerically enriched 1,2‐diols are prominent compounds that find numerous applications in organic chemistry. They are privileged building blocks for the synthesis of APIs (Active Pharmaceutical Ingredients), broadly used as chiral... more
Enantiomerically enriched 1,2‐diols are prominent compounds that find numerous applications in organic chemistry. They are privileged building blocks for the synthesis of APIs (Active Pharmaceutical Ingredients), broadly used as chiral ligands in asymmetric catalysis, and efficient auxiliaries employed to control the stereochemical outcome of total synthesis. Among the number of strategies developed for the preparation of these molecules, enzyme mediated reactions have gained a crucial role in the toolbox of organic chemists for their high efficiency and sustainability. Herein we describe a one‐pot two‐step protocol designed by combining a thiamine diphosphate (ThDP)‐dependent lyase and a NADH‐dependent reductase. The ThDP‐dependent acetoin:dichlorophenolindophenol oxidoreductase (Ao : DCPIP OR) is exploited to produce enantioenriched α‐hydroxyketones through the benzoin‐type condensation of methylacetoin with either aldehydes or activated ketones. The enantioenriched α‐hydroxyketon...
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The application of N‐heterocyclic carbene (NHC) catalysis to the polycondensation of diols and dialdehydes under oxidative conditions is herein presented for the synthesis of polyesters using fossil‐based (ethylene glycol,... more
The application of N‐heterocyclic carbene (NHC) catalysis to the polycondensation of diols and dialdehydes under oxidative conditions is herein presented for the synthesis of polyesters using fossil‐based (ethylene glycol, phthalaldehydes) and bio‐based (furan derivatives, glycerol, isosorbide) monomers. The catalytic dimethyl triazolium/1,8‐diazabicyclo[5.4.0]undec‐7‐ene couple and stoichiometric quinone oxidant afforded polyester oligomers with a number‐average molecular weight (Mn) in the range of 1.5–7.8 kg mol−1 as determined by NMR analysis. The synthesis of a higher molecular weight polyester (polyethylene terephthalate, PET) by an NHC‐promoted two‐step procedure via oligoester intermediates is also illustrated together with the catalyst‐controlled preparation of cross‐linked or linear polyesters derived from the trifunctional glycerol. The thermal properties (TGA and DSC analyses) of the synthesized oligoesters are also reported.
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Heterogeneous NHC-catalysis in batch and flow modes is an effective synthetic platform for the production of monoacylglycerols.
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A strategy for the synthesis of biologically relevant 5-hydroxy-imidazolidine-2-thione derivatives is presented. A novel class of α-sulfonylamines have been suitably prepared (46-81% yield) as precursors of formal benzylidenethiourea... more
A strategy for the synthesis of biologically relevant 5-hydroxy-imidazolidine-2-thione derivatives is presented. A novel class of α-sulfonylamines have been suitably prepared (46-81% yield) as precursors of formal benzylidenethiourea acceptors; these are generated in situ and intercepted by N-heterocyclic carbene (NHC)-activated aldehydes affording open-chain aza-benzoin-type adducts, which in turn undergo an intramolecular aza-acetalization reaction in a one-pot fashion. A thiazolium salt/triethylamine couple proved to be the more effective system to trigger the domino sequence giving the target heterocycles in good yields (45-97%) and diastereoselectivities (up to 99 : 1 dr). The multigram scale synthesis and elaboration of a selected 5-hydroxy-imidazolidine-2-thione compound is also described.
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A green scalable flow-synthesis process for the production of eugenyl acetate, an eugenol derivative with potential applications in food and medicinal chemistry, was developed.
Research Interests: Chemistry, RSC, Ion, Microreactor, Eugenol, and 3 moreIon Exchange, Packed Bed, and Ion Exchange Resin
The retention mechanism of four major carotenoids, two xanthophylls (i.e., lutein and zeaxanthin) and two carotenes (i.e., lycopene and β-carotene), was investigated in reversed-phase liquid chromatography with the aim of thermodynamic... more
The retention mechanism of four major carotenoids, two xanthophylls (i.e., lutein and zeaxanthin) and two carotenes (i.e., lycopene and β-carotene), was investigated in reversed-phase liquid chromatography with the aim of thermodynamic analysis. The experimental variables considered in this study were the composition of mobile phase (MP) and the temperature. Chromatographic elutions were undertaken under linear, isocratic conditions by using a C18 stationary phase, four different MP compositions (by varying the ratio methanol/acetonitrile from 66.5/28.5 to 47.5/47.5 v/v), and column temperatures in the range 283–313 K. Traditional Van’t Hoff analysis has been used to estimate changes of standard enthalpy (ΔH∘) and Gibbs free energy (ΔG∘) associated with the solute transfer from the mobile to the stationary phase at each mobile phase composition. The thermodynamic quantities have been correlated to the structure of investigated carotenoids and their interaction with the octadecyl sil...
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The fermentation of different sugars by Bacillus stearothermophilus ATCC 2027 to obtain 2,3-butanediol is described. Fermentation tests in shake flasks show the complete conversion of sucrose to butanediol (91% yield) and acetoin... more
The fermentation of different sugars by Bacillus stearothermophilus ATCC 2027 to obtain 2,3-butanediol is described. Fermentation tests in shake flasks show the complete conversion of sucrose to butanediol (91% yield) and acetoin (3-hydroxy-2-butanone) using a starting sugar concentration of 30 g/L. A similar result is obtained with sugar cane molasses, whereas glucose and fructose afford lower yields. Other disaccharides and monosaccharides are also tested without appreciable results. B. stearothermophilus forms a mixture of 2R,3R-butanediol and the meso isomer derived both from reduction of R-acetoin and from the butanediol cycle as demonstrated by the presence of acetoin reductase and acetylacetoin synthase.
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Recent studies have highlighted the therapeutic and ergogenic potential of the ketone body ester, (R)-3-hydroxybutyl-(R)-3-hydroxybutyrate. In the present work, the enzymatic synthesis of this biological active compound is reported. The... more
Recent studies have highlighted the therapeutic and ergogenic potential of the ketone body ester, (R)-3-hydroxybutyl-(R)-3-hydroxybutyrate. In the present work, the enzymatic synthesis of this biological active compound is reported. The (R)-3-hydroxybutyl-(R)-3-hydroxybutyrate has been produced through the transesterification of racemic ethyl 3-hydroxybutyrate with (R)-1,3-butanediol by exploiting the selectivity of Candida antarctica lipase B (CAL-B). The needed (R)-1,3-butanediol was in turn obtained from the kinetic resolution of the racemate achieved by acetylation with vinyl acetate, also in this case, thanks to the enantioselectivity of the CAL-B used as catalyst. Finally, the stereochemical inversion of the unreacted (S) enantiomers of the ethyl 3-hydroxybutyate and 1,3-butanediol accomplished by known procedure allowed to increase the overall yield of the synthetic pathway by incorporating up to 70% of the starting racemic reagents into the final product.
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A chiral NHC-catalyzed dearomatizing reaction of activated N-alkylpyridinium salts with aliphatic aldehydes is described. The resulting acylated 1,4-dihydropyridines have been obtained with complete C4 regioselectivity and... more
A chiral NHC-catalyzed dearomatizing reaction of activated N-alkylpyridinium salts with aliphatic aldehydes is described. The resulting acylated 1,4-dihydropyridines have been obtained with complete C4 regioselectivity and enantioselectivities in the range 52-78% ee. The (4R)-absolute configuration of the synthesized compounds has been determined by the TD-DFT simulation of the electronic circular dichroism spectra.
Research Interests: Biochemistry, Sociology, Chemistry, Inorganic Chemistry, Organic Chemistry, and 14 moreImmunology, Catalysis, Plant Biology, Medicine, Circular Dichroism, Ee, Configuration, Absolute Configuration, Enantioselective Synthesis, Acylation, N-alkylpyridinium salts, Regioselectivity, Heterocyclic, and Compound
The KOtBu-DMF system promotes benzoin- and Stetter-like reactions of alpha-diketone donors through a double electron-transfer-based mechanism.
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2,3-dihydroxy-2-methylbutyric acid, also known as 2,3-dimethylglyceric acid, constitutes the acyl and/or the alcoholic moiety of many bioactive natural esters. Herein, we describe a chemoenzymatic methodology which gives access to all the... more
2,3-dihydroxy-2-methylbutyric acid, also known as 2,3-dimethylglyceric acid, constitutes the acyl and/or the alcoholic moiety of many bioactive natural esters. Herein, we describe a chemoenzymatic methodology which gives access to all the four possible stereoisomers of the 2,3-dimethylglyceric acid ethyl ester. The racemic ethyl α-acetolactate, produced by the N-heterocycle carbene (NHC)-catalyzed coupling of ethyl pyruvate and methylacetoin was employed as the starting material. The racemic mixture was resolved through (S)-selective reductions, promoted by the acetylacetoin reductase (AAR) affording the resulting ethyl (2R,3S)-2,3-dimethylglycerate; the isolated remaining (S)-ethyl α-acetolactate was successively treated with baker’s yeast to obtain the corresponding (2S,3S) stereoisomer. syn-2,3-Dimethylgliceric acid ethyl ester afforded by reducing the rac-α-acetolactate with NaBH4 in the presence of ZnCl2 was kinetically resolved through selective acetylation with lipase B from ...
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Fully bio-based linear oligoesters were obtained by the unprecedented enzymatic polymerization of 5,5′-bis(hydroxymethyl)furoin with succinic and sebacic acid diethyl esters.
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ABSTRACT
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A convenient heterogeneous continuous-flow procedure for the polarity reversal of aromatic α-diketones is presented. Propaedeutic batch experiments have been initially performed to select the optimal supported base capable to initiate the... more
A convenient heterogeneous continuous-flow procedure for the polarity reversal of aromatic α-diketones is presented. Propaedeutic batch experiments have been initially performed to select the optimal supported base capable to initiate the two electron-transfer process from the carbamoyl anion of the N,N-dimethylformamide (DMF) solvent to the α-diketone and generate the corresponding enediolate active species. After having identified the 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine on polystyrene (PS-BEMP) as the suitable base, packed-bed microreactors (pressure-resistant stainless-steel columns) have been fabricated and operated to accomplish the chemoselective synthesis of aroylated α-hydroxy ketones and 2-benzoyl-1,4-diones (benzoin- and Stetter-like products, respectively) with a good level of efficiency and with a long-term stability of the packing material (up to five days).
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ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select... more
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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... Giancarlo Fantin, Marco Fogagnolo, Pier Paolo Giovannini, Alessandro Medici * and Paola Pedrini. Dipartimento di Chimica, Università di Ferrara, Via L. Borsari 46, I-44100, Ferrara, Italy. Received 26 September 1995. Available online... more
... Giancarlo Fantin, Marco Fogagnolo, Pier Paolo Giovannini, Alessandro Medici * and Paola Pedrini. Dipartimento di Chimica, Università di Ferrara, Via L. Borsari 46, I-44100, Ferrara, Italy. Received 26 September 1995. Available online 5 April 2000. Abstract. ...